9-Bromononanal → HCID 86757099, compound

HRID 1383286Notes

Reaction equation

HRID 1383286 reaction equation
[Br-].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].[Br:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH:39]=O>O1CCCC1>[Br:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]/[CH:39]=[CH:10]\[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:2]([OH:4])=[O:3]

Participants

4

Reactant 2

HCID 5433309-BromononanalHCID 11027094(6-Carboxyhexyl)triphenylphosphonium bromide

Product 1

HCID 86757099HCID 86757099, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

94 g (0.2 mol) of (6-carboxyhexyl)triphenylphosphonium bromide were suspended in 500 ml of tetrahydrofuran. 47 g (0.42 mol) of potassium t-butylate in 200 ml of tetrahydrofuran were added, followed by 50 g (0.22 mol) of 9-bromononanal. After work up and chromatography 52 g (78%) of 7Z-16-bromohexadec-7-enoic acid were obtained having the following characteristics: Z/E=90/10;

Sources & evidence

ORD record
ord-714d7c830ef147c1a2d53a1c3f646100
Source dataset
uspto-grants-2001_07
Patent number
US06255276B1

Reaction notes

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